Water → HCID 14835580, compound

Participants

Reaction Steps

Compound 9 (5 g, 17.2 mmoles) was dissolved in dioxane (11.5 ml) and a solution of sodium hydroxyde (11.5 ml, 1.5M) was added. The mixture was heated for 2 hours and poured in ice cooled water. The aqueous layer was extracted at pH 12 with Et2O (50 ml), acidified to pH 2 and reextrated with EtOAc (100 ml). This layer was dried (MgSO4), filtered and evaporated to give yellow crystals (4.2 g, 90%), after recrystallization (cyclohexane/CCl4) mp 176° C. 1H NMR (CDCl3) δ=1.25 (3H, t, J=7 Hz) 2.9 (2H, t) 3.5-3.9 (2H, m) 4.2 (2H, q, J=7 Hz) 7-7.6 (4H, m) 7.8 (1H, s). IR (CCl4) 3500-3000 (large signal) 3000 (w) 1695 (s) 1630 (w) 1600 (w) 1575 (w) 1490 (w) 1450 (w) 1410 (m) 1385 (w) 1370 (2) 1340 (w) 1320 (m). Mass spectrum m/z 261.

Provenance & Evidence